Hydrochloric Acid → HCID 178515569, compound

HRID 2165036Notes

Reaction equation

HRID 2165036 reaction equation
[OH-].[Na+].Cl.[NH2:4]O.C(O)C.Cl.[Na].O.[C:12]([CH2:20][C:21]([O:23]CC)=O)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(O)C.O.O.C(O)C>[C:13]1([C:12]2[O:19][N:4]=[C:21]([OH:23])[CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7170Ethyl benzoylacetateHCID 14798Sodium Hydroxide3×HCID 443297Hydroxyamine hydrochlorideHCID 86744058HCID 86744058, compound

Product 1

HCID 178515569HCID 178515569, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 19096565Water ethanolSolvent

Procedure

200 ml of water and 300 ml of ethanol were added to 40 g of sodium hydroxide to dissolve the sodium hydroxide. 69.5 g of hydroxylamine hydrochloride was added thereto, and the pH of the solution was adjusted to 10.0 by adding a 2N sodium hydrochloride ethanol/water (3:2) solution mixture. Under cooling with ice, 192 g of ethyl benzoylacetate and a 2N sodium hydroxide in ethanol/water (3:2) solution mixture were added dropwise simultaneously to the reaction solution so that the pH of the reaction solution was 10±0.3. After completion of the addition and stirring for 3 hours at room temperature, the reaction mixture was poured to a mixture of 500 g of concentrated hydrochloric acid and 500 g of ice, then 2.5 liters of ethanol was added to the reaction mixture and after the reaction mixture was heated for 3 hours under reflux, 2 liters of water was added thereto followed by cooling. The precipitated crystals were filtered, washed with water and dried.

Workup

  1. additionAfter completion of the addition
  2. temperatureafter the reaction mixture was heated for 3 hours
  3. temperatureunder reflux
  4. temperatureby cooling
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a4b345a91f08481caa60c6e8556985fb
Source dataset
uspto-grants-1990_07
Patent number
US04939066

Reaction notes

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